$118+ Cheap flights from Chicago (CHI) to Islip, NY (ISP)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
Oct 6 — Oct 131
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Islip with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Islip
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to IslipExplore the most affordable flight options available from Chicago to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
Explore the most affordable flight options available from Chicago to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:26 am -
1 stop8h 34m
Fri 10/236:55 pm -
1 stop13h 56m
Deal found 9/2![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:26 am -
1 stop8h 04m
Mon 10/196:55 pm -
1 stop13h 56m
Deal found 9/2![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:26 am -
1 stop8h 04m
Sun 10/186:25 pm -
1 stop14h 06m
Deal found 9/2![Frontier logo]()
$260
This Trip.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:50 pm -
1 stop24h 08m
Sat 10/106:25 pm -
1 stop14h 06m
Deal found 9/4![Frontier logo]()
$263
This CheapOair deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:51 am -
1 stop7h 05m
Sun 11/86:33 pm -
1 stop15h 13m
Deal found 9/4![Frontier logo]()
$277
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:26 am -
1 stop8h 04m
Sat 10/176:25 pm -
1 stop14h 06m
Deal found 9/5![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Thu 10/156:25 pm -
1 stop14h 06m
Deal found 9/3![Frontier logo]()
$298
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:26 am -
1 stop8h 34m
Sun 10/186:25 pm -
1 stop14h 06m
Deal found 9/1![Frontier logo]()
$301
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Mon 10/126:55 pm -
1 stop13h 56m
Deal found 9/2![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Sun 10/116:25 pm -
1 stop14h 06m
Deal found 9/2![Frontier logo]()
$311
Best flights from Chicago to IslipDiscover carefully curated flight deals from Chicago to Islip that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
Discover carefully curated flight deals from Chicago to Islip that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Sun 10/116:25 pm -
1 stop14h 06m
Deal found 9/3![Frontier logo]()
$311
This JetBlue deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:00 pm -
1 stop7h 22m
Mon 10/57:00 am -
1 stop7h 47m
Deal found 9/4![JetBlue logo]()
$527
This Orbitz deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:12 pm -
1 stop21h 33m
Tue 11/244:40 pm -
1 stop24h 12m
Deal found 9/6![Frontier logo]()
$329
This Frontier deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Mon 10/126:55 pm -
1 stop13h 56m
Deal found 9/6![Frontier logo]()
$334
This JetBlue deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
1 stop7h 22m
Mon 10/57:00 am -
1 stop7h 47m
Deal found 9/5![JetBlue logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm -
1 stop24h 08m
Tue 9/225:43 pm -
2 stops25h 40m
Deal found 9/3![Frontier logo]()
$462
This JetBlue deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:00 pm -
1 stop7h 22m
Sun 10/47:00 am -
1 stop7h 45m
Deal found 9/4![JetBlue logo]()
$527
Last-minute flights from Chicago to IslipDiscover last-minute flight deals from Chicago to Islip. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Islip. Data last updated September 6, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:50 pm -
1 stop24h 08m
Sat 10/106:25 pm -
1 stop14h 06m
Deal found 9/4![Frontier logo]()
$263
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Thu 10/156:25 pm -
1 stop14h 06m
Deal found 9/3![Frontier logo]()
$298
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Mon 10/126:55 pm -
1 stop13h 56m
Deal found 9/2![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:26 am -
1 stop8h 34m
Sun 10/116:25 pm -
1 stop14h 06m
Deal found 9/2![Frontier logo]()
$311
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:26 am -
1 stop8h 04m
Mon 10/196:55 pm -
1 stop13h 56m
Deal found 9/2![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:26 am -
1 stop8h 04m
Sun 10/186:25 pm -
1 stop14h 06m
Deal found 9/2![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:26 am -
1 stop8h 04m
Sat 10/176:25 pm -
1 stop14h 06m
Deal found 9/5![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:26 am -
1 stop8h 34m
Sun 10/186:25 pm -
1 stop14h 06m
Deal found 9/1![Frontier logo]()
$301
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:26 am -
1 stop8h 34m
Fri 10/236:55 pm -
1 stop13h 56m
Deal found 9/2![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:26 am -
1 stop8h 34m
Sun 10/256:25 pm -
1 stop14h 06m
Deal found 9/2![Frontier logo]()
$312
One-way flights from Chicago to IslipSearch for one-way flight options from Chicago to Islip. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
Search for one-way flight options from Chicago to Islip. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:51 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$118
This Expedia deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop20h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$124
This CheapOair deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:50 pm -
1 stop24h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:51 am -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:51 am -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$131
This Expedia deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm -
1 stop24h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$136
This Expedia deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop20h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:51 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$150
This Trip.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop24h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$158
This Priceline deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:46 am -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$170
Find flight deals from Chicago to Islip
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Islip (ISP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $236 (Frontier) |
One-way from | $118 (Frontier) |
Popular in | June |
Cheapest in | January |
Average price | $269 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Islip that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 6, 2026.
Use the filters below to find and compare flights from Chicago to Islip that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Fri 10/9
8:26 am-6:00 pm
1 stop8h 34m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$180
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Sun 11/1
7:50 pm-5:56 pm
2 stops21h 06m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$231
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Sun 10/18
7:44 pm-6:00 pm
2 stops21h 16m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$239
Quickest round-trip
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Fri 10/2
3:00 pm-11:22 pm
1 stop7h 22m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Wed 10/21
7:00 am-9:37 pm
1 stop13h 37m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$286
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Sat 9/26
3:00 pm-11:22 pm
1 stop7h 22m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$306
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Fri 10/9
8:26 am-6:00 pm
1 stop8h 34m
Islip Long Island
Sun 10/11
6:25 pm-7:31 am
1 stop14h 06m
$311
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Sat 11/21
5:12 pm-3:45 pm
1 stop21h 33m
Islip Long Island
Tue 11/24
4:40 pm-3:52 pm
1 stop24h 12m
$329
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Fri 10/9
8:26 am-6:00 pm
1 stop8h 34m
Islip Long Island
Mon 10/12
6:55 pm-7:51 am
1 stop13h 56m
$334
ChicagoIslip
ORD Chicago O'Hare Intl - ISP Islip Long Island
ORDISP
Chicago O'Hare Intl
Sat 10/3
7:21 pm-4:58 pm
2 stops20h 37m
Islip Long Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$335
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Chicago to Islip
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Islip in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Islip, New York flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Islip, New York flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Islip, New York flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Islip, New York flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Islip, New York flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Islip
Have a flexible travel schedule? Discover the best time to fly to Islip from Chicago with our price prediction graph.
CHI-ISP
ORD-ISP
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Islip
CHI-ISP
ORD-ISP
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Islip. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Islip?
Book flights to Islip if you plan to visit one of these locationsRiverhead
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Islip flight routes
Other flight options
Other flights from Chicago
Popular flights